It was on a patch of Ludlow St. in the East Village that Elliott Smith was formally introduced to New York artist-rager society, at bar-cum-art gallery Max Fish.

According to Elliott Smith and the Big Nothing, by Ben Nugent, Smith left a message on a friend’s answering machine saying he’d be in town in time for her birthday party. He was. “This is Elliott!” she told the crowd that night at Max Fish. “He just moved here!”

That was May of 1997. At 5 p.m. on a recent Saturday, Max Fish barkeeps were cleaning up from the night before, lining up beer bottles and wiping down the booths. The iconic neon cigarette above the venue’s door was obfuscated by construction scaffolding. “This place is a landmark,” a man in periwinkle pants said to his friend as they walked by. “It’s called Fish Bar.”

Smith once described the East Village as the place where he became a “bad alcoholic,” drinking heavily and getting into fights in the dim morning hours. It’s been widely reported that Smith moved east from Oregon in ‘97 to escape drugs and booze. Earlier that year, he had allegedly attempted suicide by jumping off a cliff in North Carolina (“It wasn’t like I made up my mind to throw myself off a cliff,” he told Spin in 2003. “I got freaked out and started running, it was totally dark, and I ran off the edge of a cliff.”) He was on the heels of two breakups—one with band Heatmiser, the other with girlfriend Joanna Bolme—and wanted to get out of Portland. So New York, where he had a handful of friends, it was.

During his New York years, Smith was more a hologram than a legend. “Elliott was hard to find,” filmmaker Steve Hanft told Blender in 2003, shortly after Smith’s death. (Hanft searched for Elliott in New York, Portland, and L.A. for his film Strange Parallel, a 30-minute promotional documentary about the singer he was hired by Dreamworks to make.) Smith was a wanderer. He was known for wandering through subway tunnels at night. He wandered in Central Park. Writer Alex Abramovich recalled running into Smith in Manhattan after seeing him perform: “We turned a corner and ran into Smith, standing alone in the drizzle, with his head down and his Walkman turned up,” he wrote in an article for Slate. “He looked unspeakably lonely.” A friend told Abramovich that he remembered seeing Smith “stumbling glumly” around the East Village. Smith’s friend Pete Krebs extrapolated for the Phoenix New Times in 2003. “A lot of his really close, old friends wouldn’t hear from him for months, years at a time,” Krebs said. “It wasn’t him being a rock star, or being too busy—Elliott kind of always had this aspect to him that was just crawling out of his own skin.”

Directly across the street from Max Fish once stood Luna Lounge, another one of Smith’s haunts. It has since relocated to Brooklyn. When asked recently why he moved the club there, part-owner Rob Sacher told the blog The Vandelles that he wanted to be where the talent was living, and that was no longer Manhattan. Ludlow between Houston and Stanton has been ravaged by the recession. “It’s a disaster,” the owner of Tre, the restaurant next door to Luna Lounge, told me. A 27-story high rise was planned for the space, but funding fell through. Next to Max Fish, the cement skeleton of multi-story boutique hotel has been erected, but nothing seems to have been added to it for months. “Everything here looks fun but is not,” my East Village friend said as we walked down the street.

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Though Smith’s memory remains tied to the East Village, he never lived there. He settled first in Jersey City before moving to Brooklyn, to the area between Park Slope proper and Gowanus. While Park Slope has long been the fabled land of colicky babies and novelists named Jonathan, three decades ago the most common street accessory in Gowanus was not a stroller but a weapon for protection. Rick Kadlub, a local tour guide whom I interviewed for an article on Brooklyn tourism, described old South Park Slope/Gowanus as something out of Night of the Living Dead, featuring the area’s junkies as zombies. By the time Smith got there, though, the area was less than feared. As Pete Hamill wrote in New York Magazine, kids from dorms had replaced kids from barracks.

Superbly grimy, Gowanus is also decidedly un-gentrifiable. Whole Foods wanted to make Gowanus the site of their first Brooklyn location, but when they broke ground in the lot they purchased at 3rd Ave. and 3rd St., they were greeted with old, drippy oil tanks and benzene-tainted soil. (Whole Foods has pledged to clean up the lot, but a store is unlikely to be built.) The Gowanus Canal, its own liquid garbage dump, courses below 2nd Ave., full of weird flotsam (wigs, Barbie dolls, Gatorade bottles), sending a curious salt air smell wafting through the region. Sometimes, Gowanus smells like Cape Cod—if Cape Cod had been doused in acid.

Priggen told me by email that Smith was a regular afternoon-goer at the bar, drinking “mostly beer and Irish whiskey.”Reading interviews, one gets the feeling Smith avoided the pomp of trendy areas. He complained more than once about the climate of Hampshire College, where he graduated in 1991. (“I just did my work,” he told Jimzine in 1997. “I liked what I studied, and I liked the classes that I took, but I couldn’t stand the atmosphere.”) In Brooklyn, Smith lived with an artist couple on Bergen St., on an elegantly worn stretch of old rowhomes that descends into Boerum Hill. Nugent, in Elliott Smith and the Big Nothing, writes that Smith was never fully comfortable living with the couple, but didn’t want to spring for his own apartment since he was touring frequently (it’s unclear if he paid rent). “He loved Shauna and Pierre but there was something wrong with every apartment … that he lived in with them,” Smith’s friend Dorien Garry told Nugent. “In one of them, he was convinced the floorboards were going to fall through and he was going to wind up like Tom Hanks in The Money Pit.”

Where Smith felt at home was O’Connor’s bar. Located on 5th Ave. near Bergen St., O’Connor’s is sandwiched between a doctor’s office and a fruit shop. It resembles a punk dungeon, with a black-painted brick facade and door held open with rusty chains. The interior is battered. Barstools are mismatched, the ceiling is cracked and stained, and leather has been ripped from booth-backs. The beer comes from bottles. The stereo blasts Flogging Molly, Johnny Cash, and The Descendents’ Suburban Home. Somehow, Smith was able to compose here, writing the bulk of his fourth album, XO, in the second booth from the door. XO would be his first work on a major label and would help catapult him to an uncomfortable fame, aided by his 1998 Oscar nomination for “Miss Misery,” which was featured, along with several of his other songs, in Good Will Hunting. At the Oscars, Smith performed “Miss Misery” as part of a lineup that included Trisha Yearwood and Celine Dion, decked out in Prada. (“I wore my own underwear,” he told a friend, according to Nugent.)

It was also at O’Connor’s that Elliott became close with bartender Spike Priggen, a musician in his own right. Priggen has been blunt about their relationship. ‘‘In the course of talking to him, I figured out that he was Elliott Smith,’’ Priggen told the New York Times shortly after Smith’s death. Priggen told me by email that Smith was a regular afternoon-goer at the bar, drinking “mostly beer and Irish whiskey.” He said he would have to double-check with another bartender about that last part, and he never wrote back. O’Connor’s used to have XO on its jukebox, but after Smith died they changed it to From a Basement on a Hill, Smith’s sixth album, released posthumously.

In an interview with CMJ not long after he moved to New York, Smith said that writing, at least when he first moved to the city, “got to a point where it was really fun.” “I didn’t make myself do it,” he said. “I didn’t really know very many people. Rather than sitting at the bar, trying not to look out of place or whatever, I would just sit there and do my own thing.” The album he wrote at O’Connor’s, XO, was released in August 1998. In 1999, he moved to L.A. in another attempt at detoxing. He died there in 2003.

L.A. made him uncomfortable, Smith told Jimzine. “All these falsely tan people with great abs, that, you know, wear impossible clothes.” Not that he was comfortable anywhere. In 1997, Smith told Greg Dwinnell of Eggbert Records that he considered Portland his home, or maybe D.C., but the truth was he was never really anywhere for more than two weeks. In New York, though, he felt he could blend. He fit in, if not for very long.

“There’s just more people that look like I do,” he said in another 1997 interview. “There’s always much bigger freaks than me in New York, you know, on every block.”